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S-444,823

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
S-444,823
Clinical data
ATC code
  • none
Identifiers
  • 3-(2-(1-(cyclohexylmethyl)-2-oxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carboxamido)thiazol-4-yl)propanoic acid
CAS Number
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC25H33N3O4S
Molar mass471.62 g·mol−1
3D model (JSmol)
  • O=C(C(C(NC1=NC(CCC(O)=O)=CS1)=O)=C2)N(CC3CCCCC3)C4=C2CCCCCC4
  • InChI=1S/C25H33N3O4S/c29-22(30)13-12-19-16-33-25(26-19)27-23(31)20-14-18-10-6-1-2-7-11-21(18)28(24(20)32)15-17-8-4-3-5-9-17/h14,16-17H,1-13,15H2,(H,29,30)(H,26,27,31)
  • Key:SYBONVBDFTYUQP-UHFFFAOYSA-N

S-444,823 is a drug developed byShionogi which is acannabinoid agonist.[1] It was developed as anantipruritic, and has moderate selectivity for theCB2 subtype, having a CB2 affinity of 18nM, and 32x selectivity over theCB1 receptor. In animal studies it showed analgesic effects and strongly reduced itching responses, but without producing side effects such assedation andcatalepsy that are seen with centrally acting CB1 agonists.[2]

See also

[edit]

References

[edit]
  1. ^Arimura A. Novel Use of Cannabinoid Receptor Agonist. Patent WO 2005/016351
  2. ^Odan M, Ishizuka N, Hiramatsu Y, Inagaki M, Hashizume H, Fujii Y, et al. (April 2012). "Discovery of S-444823, a potent CB1/CB2 dual agonist as an antipruritic agent".Bioorganic & Medicinal Chemistry Letters.22 (8):2898–901.doi:10.1016/j.bmcl.2012.02.050.PMID 22421019.
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers

(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)


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